2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-one O-tosyl oxime | 629646-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-one O-tosyl oxime
• 英文别名: [[2,2,2-Trifluoro-1-(3-nitrophenyl)ethylidene]amino] 4-methylbenzenesulfonate；[[2,2,2-trifluoro-1-(3-nitrophenyl)ethylidene]amino] 4-methylbenzenesulfonate
• CAS: 629646-11-3
• 化学式: C₁₅H₁₁F₃N₂O₅S
• 分子量: 388.324
• InChiKey: INMHGEFTKASFMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  95-98 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  446.3±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-one O-tosyl oxime 在 sodium dithionite 、 氨 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 重水 为溶剂， 反应 42.0h， 生成 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline
  参考文献：
  名称：

  NLRP3抑制剂重氮嗪光亲和探针的设计，合成和评估

  摘要：

  NLRP3抑制剂MCC950 / CRID3可改善动物模型中的大量炎症性疾病。在本文中，我们描述了一种称为TPD-950-Br的三氟甲基苯基重氮（TPD）光亲和探针，以探测MCC950的分子相互作用。我们显示，TPD-950-Br在NLRP3抑制剂检测中共激活并在光活化后捕获近端物质，并抑制IL-1β的产生。

  DOI：

  10.1016/j.tetlet.2020.151849
• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 盐酸羟胺 、 硝酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-one O-tosyl oxime
  参考文献：
  名称：

  NLRP3抑制剂重氮嗪光亲和探针的设计，合成和评估

  摘要：

  NLRP3抑制剂MCC950 / CRID3可改善动物模型中的大量炎症性疾病。在本文中，我们描述了一种称为TPD-950-Br的三氟甲基苯基重氮（TPD）光亲和探针，以探测MCC950的分子相互作用。我们显示，TPD-950-Br在NLRP3抑制剂检测中共激活并在光活化后捕获近端物质，并抑制IL-1β的产生。

  DOI：

  10.1016/j.tetlet.2020.151849

文献信息

• Alternative One-Pot Synthesis of (Trifluoromethyl)phenyldiazirines from Tosyloxime Derivatives: Application for New Synthesis of Optically Pure Diazirinylphenylalanines for Photoaffinity Labeling
  作者：Lei Wang、Yuta Murai、Takuma Yoshida、Akiko Ishida、Katsuyoshi Masuda、Yasuko Sakihama、Yasuyuki Hashidoko、Yasumaru Hatanaka、Makoto Hashimoto

  DOI：10.1021/ol503630z

  日期：2015.2.6

  Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2– is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.

  开发了由相应的甲苯磺肟肟形成的另一种一锅法合成3-（三氟甲基）-3-苯基重氮基衍生物。中间diaziridine的由NH去质子化2 -是用于施工二吖丙因的新方法。而且，尝试了涉及这些方法的光学纯的（三氟甲基）二氮杂基苯基丙氨酸衍生物的新型合成。
• [EN] SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME<br/>[FR] SULFONYLURÉES, COMPOSÉS APPARENTÉS, ET LEUR UTILISATION
  申请人：UNIV QUEENSLAND

  公开号：WO2016131098A8

  公开（公告）日：2017-03-16
• Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase
  作者：Barbara Biasotti、Sabrina Dallavalle、Lucio Merlini、Carlo Farina、Stefania Gagliardi、Carlo Parini、Pietro Belfiore

  DOI：10.1016/s0968-0896(03)00106-8

  日期：2003.5

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：US20180044287A1

  公开（公告）日：2018-02-15

  The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.